Overstories, Understories, and the Messy Middle: How Leaders Cultivate Healthy Organizations

When Scott Brown set out to unravel what makes organizations truly healthy, he stumbled upon a paradox. For decades, we've treated businesses, industries, and teams as machines, systems to calibrate and control. But what if they're not machines at all? What if they are ecosystems ... living, breathing, interdependent ecosystems?
In Overstories, Understories, and The Messy Middle, Brown argues that every organization is defined by its overstory; the canopy of beliefs, assumptions, values, narratives, and aspirations that explain why it exists. But an overstory alone is not enough. We live in our organization's understory; the everyday rituals, relationships, and practices that define our days. The interconnectedness of these two stories forms our organization's culture. Not the culture publicly espoused in marketing materials, but the one felt in quiet hallways and late-night emails. And between these two layers lies the messy middle, that place where leaders grow relationships.
Brown shows us that organizational collapse rarely happens because of a single catastrophic decision. Collapse begins when the overstory stops nurturing the understory, and when the understory can no longer support the overstory. Through vivid storytelling, he takes readers inside the decaying steel mills of Pittsburgh, the shuttered aisles of once-great retailers, and the silent workplaces ruled by bad bosses. He explores why everyone knows what it feels like to work for a bad boss, yet few ever admit to being one.
But this is not just a critique. Brown offers a path forward. He argues that leadership is not granted through title or authority. It is earned by those who create the conditions necessary for ecosystems to thrive. Leaders, he suggests, must become gardeners, cultivating the stories, artifacts, and rituals that weave strong overstories with fertile understories. Only then can organizations become places where people don't just comply but commit and create.
Drawing on two decades managing retail teams and fifteen years coaching executives, Brown outlines four requirements for leaders seeking to regenerate healthy ecosystems:
First, leaders must bridge the gap between intention and action. Bad bosses aren't born; they're made ... and so are leaders. The journey begins by stepping beyond the comfortable world of "what is" to embrace the unsettling possibilities of "what if."
Second, change is not an event but a function of habits. Shifting collective behaviors and mindsets requires disrupting the status quo with new stories, artifacts, and rituals that reshape what people believe and do.
Third, leaders must curate culture as context. Like a Newton's Cradle transferring energy seamlessly across its orbs, healthy cultures create momentum through alignment. Friction emerges only when leaders allow misalignment between what people do, say, value, and aspire to become.
Finally, leaders must choose to play a different game. Business framed as zero-sum games misses the opportunity to rewrite the rules entirely. Great leaders cultivate formal and adaptable games where collaboration, creativity, and collective wins become possible.
This is not just a book about what leaders should do. It is a book about how they should think. It is also a book about how leaders should think ... about ecosystems, not hierarchies; about alignment, not authority; about cultivating what is possible, rather than managing what is convenient. In a world starved for workplaces where people thrive rather than merely survive, Brown's message is both timely and timeless.